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19 Greentree Lane, Chester, NY 10918

$3,400,000
  • 19 Greentree Lane, Chester, NY 10918 Main Photo

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New to the Market Active
BEDS4 BATHS4 full SQUARE FEET7,750 MLS#988789
STATUSActive PROPERTY TYPEResidential - Single Family SCHOOLChester

Property Description

Set behind a gated entrance with a private guard house and unfolding across 8.4 private acres, The Retreat at Greentree is a true estate in every sense, engineered for privacy, designed for lifestyle, and positioned as one of the most unique offerings in the Hudson Valley.A cascading waterfall greets you on arrival, establishing a sense of calm and separation from the outside world. From that moment forward, every detail reinforces the same idea. This property was built intentionally, without compromise.Originally designed by renowned architect Paul Rudolph, the residence carries a level of architectural pedigree rarely available. Spanning over 7,750 square feet, the home blends that design legacy with modern performance, including radiant heated floors, geothermal systems, and thoughtfully curated living spaces that feel both refined and highly functional.What truly sets this property apart is the lifestyle it delivers.A private helipad offers direct access to Manhattan in approximately 14 minutes, redefining convenience at the highest level. The grounds unfold as a resort-caliber setting, anchored by a heated saltwater pool, three private cabanas, and a fully equipped outdoor kitchen with a dedicated dining space designed for effortless indoor outdoor living. A rare white sand beach introduces an unexpected element, creating a setting that feels more like a destination resort than a private residence.Inside, the home takes on a spa-like atmosphere, with wellness-driven features including a private sauna and spaces designed to restore and recharge. The primary suite is its own retreat, complete with a three-season room that extends the experience outdoors while maintaining complete privacy. A fully built-out home theater adds another layer to the lifestyle, bringing a true cinematic environment into the comfort of your own home.Beyond the property itself, the location adds another dimension. This is the perfect getaway for winter weekends, fall retreats, or summer escapes, surrounded by some of the Hudson Valley's most sought-after destinations. Just minutes from LEGOLAND New York Resort, Woodbury Common Premium Outlets, Warwick Valley Winery & Distillery, local apple orchards throughout Warwick, Bear Mountain State Park for skiing and outdoor recreation, and the five-star Glenmere Mansion, the area offers a rare blend of recreation, luxury, and accessibility. Hiking, camping, fishing, skiing, biking, horseback riding, fine dining, and shopping are all within reach, creating a year-round lifestyle that

19 Greentree Lane | MLS# 988789

This single family home located at 19 Greentree Lane, Chester, NY 10918 is currently listed for sale with an asking price of $3,400,000. This property was built in 1986 and has 4 bedrooms and 4 full baths with 7750 sq. ft. Greentree Lane is located within the Chester school district. Search Chester real estate on dshea.coachrealtors.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Central Air
Fireplaces: 1
Garage: 2
Heating: Geothermal, Radiant Floor
Home Style: Contemporary, Estate
Lot Size: 8.40 Acres
Taxes: $30,891
Year Built: 1986

Amenities

Built-in Features
Cathedral Ceiling(s)
Chefs Kitchen
Eat-in Kitchen
Entertainment Cabinets
Entrance Foyer
Formal Dining
High Speed Internet
Kitchen Island
Natural Woodwork
Open Kitchen
Original Details
Pantry
Primary Bathroom
Quartz/Quartzite Counters
Recessed Lighting
Walk-In Closet(s)
Washer/Dryer Hookup

Feature Descriptions

Appliances: Dishwasher, Dryer, Freezer, Oven, Range, Refrigerator, Washer, Wine Refrigerator
Building Area Total: 8200
Days on Site: 6
Exterior: Wood Siding
Fireplace Features: Family Room, Free Standing
Flooring: Hardwood, Wood
Formal Dining: Yes
GarageY/N: Yes
Laundry: Laundry Room
Number Of Kitchens: 2
On Market Date: 2026-04-29
Parcel Number: 332089-038-000-0001-066.100-0000
Parking Features: Driveway, Garage, Off Street, Private
Rental Term: Monthly
Rooms Total: 16
Sewer: Septic Tank
Swimming Pool: Yes
Utilities: Cable Connected, Electricity Connected, Phone Connected, Propane, Water Connected
Water: Well

Local Schools

High School: Chester Academy-Middle/High School
Middle School: Chester Academy-Middle/High School
Elementary School: Chester Elementary School
School District: Chester

Listed By / Shown By

Listing By

Agency Name: Serhant LLC
Agency Phone: 646-480-7665

Shown By

Agent Name: Donald Shea
Agent Phone: (516) 512-4876
Agency Title: Howard Hanna | Coach Realtors

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Estimated Payment

$ 18,167.46 per month $14,601.55 Principal & Interest $2,574.25 Property Tax $991.67 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 04/30/2026. The listing information on this page last changed on 04/30/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Thu 04/30/2026 1:36:04 AM EST) or OneKey MLS (last updated Thu 04/30/2026 1:31:18 AM EST). Real estate listings held by brokerage firms other than Howard Hanna | Coach Realtors may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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